The specific goal of this research proposal is the total synthesis of the indoline alkaloid communesin B. Communesin B is a broadly biologically active natural product that posseses two vicinal quaternary centers and two aminal moeities embedded within a heptacyclic framework. There have been no reported total syntheses to date. The successful synthesis of this compound would represent an important advance in the field of alkaloid synthesis. The key step in the synthesis of communesin B would be a Mo-, Ir-, or W- catalyzed asymmetric allylic alkylation (AAA) reaction which will employ indole derivatives as the nucleophile. The use of indoles nucleophiles in the AAA reaction has not been precedented and would be a significant extension of the current AAA technology. [unreadable] [unreadable] [unreadable]